Benzyl Alcohol → Benzyl Alcohol

HRID 1049068Notes

Reaction equation

HRID 1049068 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:23]=[CH:24][C:25]3[O:29][C:28]([C:30](=[O:32])[NH2:31])=[CH:27][C:26]=3[CH:33]=2)[CH2:18][CH2:17]1)#[N:2].[ClH:34].[CH2:35]([OH:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>>[ClH:34].[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][N:19]([C:22]2[CH:23]=[CH:24][C:25]3[O:29][C:28]([C:30](=[O:32])[NH2:31])=[CH:27][C:26]=3[CH:33]=2)[CH2:20][CH2:21]1)#[N:2].[CH2:35]([OH:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 6918314Vilazodone

Product 2

HCID 244Benzyl AlcoholHCID 69183132-benzofurancarboxamide, 5-(4-(4-(5-cyano-1H-indol-3-yl)butyl)-1-piperazinyl)-, hydrochloride (1:1)

Conditions

Temperature
22.5 °C

Procedure

1-[4-(5-Cyanoindol-3-yl)butyl]-4-(2-carbamoyl-benzofuran-5-yl)-piperazine (1 g) was dissolved in benzyl alcohol (10 ml) under inert gas atmosphere at 20-25° C. To the clear solution was added conc. HCl (0.31 g). The resulting suspension was stirred for 20 h at 20-25° C. The suspension was heated to 35° C. and maintained for 3 h. The solid was filtered, washed with MTBE (2×5 ml) and dried at 65° C. to afford 0.65 g hemi solvate of 1-[4-(5-cyanoindol-3-yl)butyl]-4-(2-carbamoyl-benzofuran-5-yl)-piperazine hydrochloride with benzyl alcohol.

Workup

  1. temperatureThe suspension was heated to 35° C.
  2. temperaturemaintained for 3 h
  3. filtrationThe solid was filtered
  4. washwashed with MTBE (2×5 ml)
  5. customdried at 65° C.

Sources & evidence

ORD record
ord-4f73736341ea483eaa4b50989051dd1e
Source dataset
uspto-grants-2016_07
Patent number
US09382233B2

Reaction notes

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